Toward multifunctional anticancer therapeutics: post-synthetic carbonate functionalisation of asymmetric Au(i) bis-N-heterocyclic carbenes

Chem Commun (Camb). 2020 Jul 21;56(57):7877-7880. doi: 10.1039/d0cc03339a. Epub 2020 Jun 10.

Abstract

A post-synthetic strategy is reported that allows for functionalisation of Au(i)-bis NHCs via carbonate formation. The scope of this methodology was explored using both aromatic and aliphatic alcohols. As a demonstration of potential utility, the fluorescent Au(i)-bis NHC conjugate 5 was prepared; it was found to have enhanced stability when formulated with bovine serum albumin, localise within the mitochondria of A549 cells and do so without compromising the high cytotoxicity seen for the parent Au(i)-bis NHC system.

MeSH terms

  • A549 Cells
  • Antineoplastic Agents / chemical synthesis
  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / pharmacology*
  • Cell Proliferation / drug effects
  • Coordination Complexes / chemical synthesis
  • Coordination Complexes / chemistry
  • Coordination Complexes / pharmacology*
  • Drug Screening Assays, Antitumor
  • Gold / chemistry
  • Gold / pharmacology*
  • Heterocyclic Compounds / chemistry
  • Heterocyclic Compounds / pharmacology*
  • Humans
  • Methane / analogs & derivatives*
  • Methane / chemistry
  • Methane / pharmacology
  • Molecular Structure
  • Optical Imaging

Substances

  • Antineoplastic Agents
  • Coordination Complexes
  • Heterocyclic Compounds
  • carbene
  • Gold
  • Methane